Happy Friday, gang! There’s something magical about early October evenings; the air turns crisp, the light softens, and it feels like the season is inviting us to slow down. This week on Fridays with Oscar, we’re savoring that autumn mood with two simple pleasures: a Fig Bourbon Smash that tastes like fall in a glass, and a Caramelized Onion & Pear Flatbread that’s equal parts cozy and elegant. And because no evening is complete without a little style inspiration, Kelly and I are sharing layered looks perfect for early October recipes and style over 50.
🍂 This Week on Fridays with Oscar 🐾
- A Fig Bourbon Smash cocktail that captures the essence of fall in every sip
- A Caramelized Onion & Pear Flatbread that’s sweet, savory, and perfect for cool nights
- Tips for prepping and pairing your dishes for easy, elegant entertaining
- A cozy check-in with Oscar and Ollie, our favorite furry fall companions
- Inspiration for embracing Fall Recipes & Style with confidence and charm
Fall Recipe: Fig Smash & Caramelized Onion Flatbread
🥃 Cocktail First: Fig Bourbon Smash
If fall had a flavor, this would be it. Earthy figs meet smooth bourbon and bright lemon for a cocktail that’s as beautiful as it is delicious. The touch of honey adds warmth, while fresh thyme gives it that unmistakable autumn aroma. It’s the perfect drink to sip by the setting sun—simple to make, yet wonderfully sophisticated for early October gatherings.
Frequently Asked Questions
🥃 Fig Bourbon Smash
Q1: What type of bourbon works best for this cocktail?
A: Choose a smooth, mid-range bourbon—something with a hint of caramel or vanilla. It complements the sweetness of the figs and honey beautifully without overpowering the drink.
Q2: Can I make this cocktail ahead of time?
A: Absolutely. You can muddle the figs, lemon juice, honey, and thyme a few hours early. Just keep the mixture chilled and add the bourbon and ice right before serving.
Q3: What can I use if I don’t have fresh figs?
A: Dried figs work in a pinch! Soak them in hot water for about 10 minutes to soften, then muddle as directed. The flavor will be slightly deeper and richer—perfect for cooler evenings.
- 4 oz bourbon
- 2 fresh figs quartered (plus more for garnish)
- 1 oz fresh lemon juice
- 1 oz honey or simple syrup
- 4 –6 fresh thyme sprigs
- Ice
- Club soda optional, for topping
In a cocktail shaker, muddle figs with lemon juice, honey, and thyme sprigs until well combined.
Add bourbon and ice, then shake vigorously for 15–20 seconds.
Strain into 2 rocks glasses filled with ice.
Top with a splash of club soda if you prefer a lighter drink.
Garnish with a fig slice and fresh thyme sprig.
🍐 Caramelized Onion & Pear Flatbread
This flatbread brings together everything I love about fall cooking: cozy flavors, golden edges, and just the right mix of sweet and savory. Caramelized onions lend a rich depth, while ripe pears, tangy cheese, and toasted walnuts add layers of flavor that feel both rustic and refined. Drizzled with honey and topped with fresh arugula, it’s an easy recipe that feels special enough for a Friday evening on the porch.
Frequently Asked Questions
🍐 Caramelized Onion & Pear Flatbread
Q1: Can I make this flatbread ahead of time?
A: Yes, you can caramelize the onions and prep the toppings earlier in the day. Assemble and bake right before serving for the freshest flavor and crispest crust.
Q2: What cheese works best if I don’t like gorgonzola?
A: Goat cheese is a great substitute; it’s milder and creamy, with a slight tang that still pairs beautifully with the pears and honey drizzle.
Q3: Can I use another type of crust besides flatbread or naan?
A: Of course! Puff pastry or a pre-baked pizza crust both work well. Just adjust the baking time slightly, about 2–3 minutes less for puff pastry.
- 1 store-bought flatbread or pizza crust naan works beautifully
- 2 tbsp olive oil
- 1 large yellow onion thinly sliced
- 1 ripe pear thinly sliced
- 1/2 cup crumbled gorgonzola or goat cheese if preferred
- 1/2 cup shredded mozzarella
- 2 tsp fresh thyme leaves
- 1/4 cup walnuts toasted and chopped
- Honey for drizzling
- Fresh arugula for garnish
Preheat oven to 400°F. Place flatbread on a parchment-lined baking sheet.
In a skillet over medium heat, warm olive oil. Add sliced onion and cook, stirring occasionally, until deeply caramelized (about 20–25 minutes).
Spread caramelized onions evenly over the flatbread. Layer with pear slices, gorgonzola, mozzarella, and thyme.
Bake for 10–12 minutes, until cheese is melted and bubbly.
Remove from oven and top with toasted walnuts, a drizzle of honey, and a handful of fresh arugula.
Slice and serve warm.
🐾 While mixing, baking, and tasting our way through fall’s best flavors, Kelly and I stayed comfortable and stylish in cozy layers that echo the warmth of the season. Think soft knits, rich textures, and easy silhouettes that move with you in the kitchen but still look polished for guests. These looks prove that early October recipes and style over 50 pair together perfectly.
Beth’s Outfit: Fall Layers That Shine
Complete the look with slingback pumps and a mother-of-pearl necklace for just the right touch of shine.
Shop Beth’s Look
Kelly’s Outfit: Effortless Fall Neutrals
Mary Jane ballet flats add polish while staying comfortable enough for entertaining or an evening stroll.
Shop Kelly’s Look
🐾 Cheers to Fall Recipes!
As the nights grow cooler, I love nothing more than layering up, lighting a few lanterns, and sipping something seasonal on the porch. Our Fall Recipe: The Fig Bourbon Smash and Caramelized Onion & Pear Flatbread make the perfect pairing for early October evenings—simple, elegant, and full of fall flavor.
For More Autumnal Inspiration, check out: Harvest Table: Trader Joe’s Appetizers & Fall Style.
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